Fullerene and its derivatives have attracted attention in the fields of cluster science relating to clathrates and application to pharmaceuticals and photoelectronic devices. Of these, fullerene 1,3-dioxolane is an electron acceptor and has attracted attention as a high-functionality material.
The method of manufacturing 1,3-dioxolane by the reaction below from an epoxide and a carbonyl compound is known. The use of a Lewis acid catalyst in this reaction has been proposed.
For example, the method of manufacturing 1,3-dioxolane by the following reaction employing BF3 etherate as a catalyst is described in Reference 1 (B. N. Blackett, J. M. Coxon., M. P. Hartshorn, A. J. Lewis, G. R. Little and G. J. Wright, Tetrahedron, 26, 1311-1313 (1970)).

Further, the method of manufacturing 1,3-dioxolane by the following reaction using anhydrous CuSO4 as a catalyst is described in Reference 2 (R. P. Hanzlik and M. Leinwetter. J. Org. Chem., 43, 438 (1978)).

The method of manufacturing 1,3-dioxolane by the following reaction is described in Reference 3 (H. Steinbrink, Ger. Patent (DOS) 1086241, Chemische Werke Hüls AG (1959)).

The method of manufacturing 1,3-dioxolane by the reaction is described in Reference 4 (F. Nerdel, J. Buddrus, G. Scherowsky, D. Klamann, and M. Fligge, Justus Liebig Ann. Chem. 710, 85 (1967)).
As catalysts, KSF clay is employed in Reference 3 and tetraethylammonium bromide is employed in Reference 4.
The mechanisms of the reactions described in the above-cited references are as follows. Due to the stereochemistry of products obtained by the method described in Reference 1 and based on the results of tests employing 018 acetone, as is indicated below, it is thought that following a backside attack by the carbonyl oxygen, the CC bond is rotated, producing a second CO bond and thereby producing 1,3-dioxolane. However, in this reaction, there is a problem in that a side reaction of epoxy and aldehyde reduces the yield of 1,3-dioxolane. Further, the catalyst employed is highly hygroscopic and difficult to handle.

A method for manufacturing 1,3-dioxolane by the following reaction using a pyridinium salt as a catalyst is described in Reference 5 (S-B. Lee, T. Tanaka, and T. Endo, Chem. Lett., 2019-2022 (1990)).
The reaction mechanism of the method described in Reference 5 is presumed to be similar to that set forth above.
References 6 to 8 report methods of obtaining fullerene 1,3-dioxolane using fullerene as a starting material (Reference 6: Y. Achiba et al., Tetrahedron Lett., 34, 7629-7632 (1993); Reference 7: C. S. Foote et al., Angew. Chem. Int. Ed. 31, 351-353 (1992); Reference 8: S-H. Wu et al., J. Chem. Soc., Chem. Commun., 1995, 1071). However, in the methods described in References 6 to 8, fullerene 1,3-dioxolane is often obtained together with other fullerene derivatives. Thus, these methods do not permit the obtaining of fullerene 1,3-dioxolane with high yields. There is a further problem in that the reagents employed, such as peroxides, are difficult to handle.